Exam_3_Green - CEM251/Fall 2010/Third Hourly Exam(page 1(12...

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CEM251/Fall 2010/Third Hourly Exam. ...... (page 1) (12 points total) 1. Draw the structure of the major organic product of the following reactions: C H C CH CH 3 CH 3 a) 2 pts. H 2 , Pt (excess) b) 2 pts. Na, NH 3 C show stereochemistry CH 2 CH 3 C CH 3 c) 2 pts. H 2 , Pd, , Quinoline show stereochemistry Pb(OAc) 2 C CH 3 C CH CH 3 CH 3 d) 2 pts. Pt show stereochemistry D 2 (deuterium) CH 3 H 2. a) (2 pts.) (2 pts.) A B Which of the above olefins ( A, B or C ) has the highest heat of hydrogenation? b) Which of the above olefins ( A, B or C ) has the lowest heat of hydrogenation? C CH 2 CH 3 CH CH 2 CH 3 CH 2
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CEM251/Fall 2010/Third Hourly Exam. ...... (page 2) (15 points total) 1. Draw the structure of the major organic product of the following reactions: CH 2 CH 2 OH a) 2 pts. CrO 3 , H 2 SO 4 (excess) b) 2 pts. LiAlH 4 H 3 O + 1) 2) CH 2 CH 3 (excess) C OH O c) 2 pts. NaBH 4 2 pts. H 3 O + 1) 2) C O CrO 3 , H 2 SO 4 CH 2 H (excess) d) 2 pts. CrO 3 (pcc) HCl pyridine CH 2 OH CH 3 CH 2 CH 2 e) 2 pts.
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Exam_3_Green - CEM251/Fall 2010/Third Hourly Exam(page 1(12...

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